NPASS Compound

Structure

CID85772 OpenBabel06191715422D 25 25 0 0 1 0 0 0 0 0999 V2000 2.1180 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6180 -3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6399 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8115 -1.0976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8604 -0.7885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1180 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8090 -2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6036 -0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -4.0287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 2.1100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5817 0.0885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 2 0 0 0 0 3 15 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 14 17 1 0 0 0 0 15 21 2 0 0 0 0 16 15 1 1 0 0 0 16 18 1 0 0 0 0 17 22 2 0 0 0 0 18 25 1 1 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	374.052
LogP:	2.036
LogD:	2.09
LogS:	-3.717
# Rotatable Bonds:	5
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	4.59
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.496
MDCK Permeability:	2.3171491193352267e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.543
Plasma Protein Binding (PPB):	75.81208038330078%
Volume Distribution (VD):	0.318
Pgp-substrate:	25.5939998626709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.684
CYP2C19-substrate:	0.198
CYP2C9-inhibitor:	0.757
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.178
CYP2D6-substrate:	0.803
CYP3A4-inhibitor:	0.536
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	8.298
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.313
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.514
Maximum Recommended Daily Dose:	0.203
Skin Sensitization:	0.611
Carcinogencity:	0.247
Eye Corrosion:	0.447
Eye Irritation:	0.064
Respiratory Toxicity:	0.699

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC85772

Natural Product ID:	NPC85772
*Common Name:**	(E)-((1S,10R,E)-10-Acetyl-3-Methyl-7-Methylene-6-Oxocyclodec-2-Enyl) 4-Hydroxy-4-Methylpent-2-Enoate
IUPAC Name:	[(1S,2E,10R)-10-acetyl-3-methyl-7-methylidene-6-oxocyclodec-2-en-1-yl] (E)-4-hydroxy-4-methylpent-2-enoate
Synonyms:
Standard InCHIKey:	WNLDPFSWPBREOU-SURQFZOFSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-13-6-9-17(22)14(2)7-8-16(15(3)21)18(12-13)25-19(23)10-11-20(4,5)24/h10-12,16,18,24H,2,6-9H2,1,3-5H3/b11-10+,13-12+/t16-,18-/m0/s1
SMILES:	O=C(O[C@H]1/C=C(C)/CCC(=O)C(=C)CC[C@H]1C(=O)C)/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465964
PubChem CID:	11703004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30388	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180813]
NPO32969	eunicea sp.	Species	Plexauridae	Eukaryota	n.a.	Caribbean gorgonian coral	n.a.	PMID[16180813]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	16.0	ug.mL-1	PMID[568651]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC85772 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1213
0.2-0.3	5457
0.3-0.4	11887
0.4-0.5	13478
0.5-0.6	6302
0.6-0.7	3306
0.7-0.8	791
0.8-0.85	69
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC261380
0.8471	Intermediate Similarity	NPC72513
0.8452	Intermediate Similarity	NPC125290
0.8452	Intermediate Similarity	NPC470755
0.8415	Intermediate Similarity	NPC325031
0.8391	Intermediate Similarity	NPC144133
0.8391	Intermediate Similarity	NPC179394
0.8372	Intermediate Similarity	NPC476805
0.8353	Intermediate Similarity	NPC305475
0.8353	Intermediate Similarity	NPC315395
0.8353	Intermediate Similarity	NPC475461
0.8353	Intermediate Similarity	NPC234038
0.8353	Intermediate Similarity	NPC316426
0.8353	Intermediate Similarity	NPC261721
0.8333	Intermediate Similarity	NPC158756
0.8333	Intermediate Similarity	NPC96259
0.8333	Intermediate Similarity	NPC141193
0.8295	Intermediate Similarity	NPC261607
0.8295	Intermediate Similarity	NPC300312
0.8295	Intermediate Similarity	NPC111114
0.8272	Intermediate Similarity	NPC93763
0.8272	Intermediate Similarity	NPC128276
0.8272	Intermediate Similarity	NPC108816
0.8272	Intermediate Similarity	NPC267231
0.8235	Intermediate Similarity	NPC255307
0.8214	Intermediate Similarity	NPC40746
0.8214	Intermediate Similarity	NPC169575
0.8214	Intermediate Similarity	NPC16488
0.8182	Intermediate Similarity	NPC145666
0.8182	Intermediate Similarity	NPC475855
0.8171	Intermediate Similarity	NPC270126
0.8161	Intermediate Similarity	NPC476803
0.8161	Intermediate Similarity	NPC475819
0.8148	Intermediate Similarity	NPC57744
0.814	Intermediate Similarity	NPC469910
0.814	Intermediate Similarity	NPC279859
0.814	Intermediate Similarity	NPC38576
0.814	Intermediate Similarity	NPC469483
0.814	Intermediate Similarity	NPC122502
0.8132	Intermediate Similarity	NPC230800
0.8125	Intermediate Similarity	NPC155587
0.8118	Intermediate Similarity	NPC14575
0.8118	Intermediate Similarity	NPC191476
0.8118	Intermediate Similarity	NPC476804
0.8118	Intermediate Similarity	NPC70424
0.8118	Intermediate Similarity	NPC196487
0.8118	Intermediate Similarity	NPC114979
0.8118	Intermediate Similarity	NPC243618
0.8111	Intermediate Similarity	NPC65829
0.8111	Intermediate Similarity	NPC469632
0.8111	Intermediate Similarity	NPC167219
0.8101	Intermediate Similarity	NPC275098
0.8095	Intermediate Similarity	NPC474291
0.8068	Intermediate Similarity	NPC106040
0.8068	Intermediate Similarity	NPC212598
0.8068	Intermediate Similarity	NPC115179
0.8049	Intermediate Similarity	NPC471465
0.8049	Intermediate Similarity	NPC196653
0.8049	Intermediate Similarity	NPC192006
0.8046	Intermediate Similarity	NPC478144
0.8046	Intermediate Similarity	NPC160138
0.8046	Intermediate Similarity	NPC478145
0.8025	Intermediate Similarity	NPC235906
0.8023	Intermediate Similarity	NPC11804
0.8	Intermediate Similarity	NPC473390
0.8	Intermediate Similarity	NPC131669
0.8	Intermediate Similarity	NPC318468
0.8	Intermediate Similarity	NPC469645
0.8	Intermediate Similarity	NPC161045
0.8	Intermediate Similarity	NPC474703
0.8	Intermediate Similarity	NPC475947
0.8	Intermediate Similarity	NPC125674
0.8	Intermediate Similarity	NPC475838
0.8	Intermediate Similarity	NPC228451
0.8	Intermediate Similarity	NPC476355
0.8	Intermediate Similarity	NPC250315
0.8	Intermediate Similarity	NPC469692
0.8	Intermediate Similarity	NPC475302
0.7978	Intermediate Similarity	NPC77337
0.7978	Intermediate Similarity	NPC473448
0.7976	Intermediate Similarity	NPC24417
0.7976	Intermediate Similarity	NPC112868
0.7976	Intermediate Similarity	NPC42470
0.7976	Intermediate Similarity	NPC471325
0.7957	Intermediate Similarity	NPC316598
0.7955	Intermediate Similarity	NPC469628
0.7955	Intermediate Similarity	NPC471047
0.7955	Intermediate Similarity	NPC260343
0.7955	Intermediate Similarity	NPC469653
0.7955	Intermediate Similarity	NPC469631
0.7955	Intermediate Similarity	NPC475906
0.7952	Intermediate Similarity	NPC469617
0.7952	Intermediate Similarity	NPC178277
0.7952	Intermediate Similarity	NPC89128
0.7931	Intermediate Similarity	NPC150755
0.7927	Intermediate Similarity	NPC316324
0.7927	Intermediate Similarity	NPC474760
0.7927	Intermediate Similarity	NPC7563
0.7927	Intermediate Similarity	NPC141789
0.7927	Intermediate Similarity	NPC116177
0.7927	Intermediate Similarity	NPC171204
0.7927	Intermediate Similarity	NPC320630
0.7927	Intermediate Similarity	NPC476028
0.7912	Intermediate Similarity	NPC474247
0.7912	Intermediate Similarity	NPC121825
0.7901	Intermediate Similarity	NPC329852
0.7901	Intermediate Similarity	NPC244166
0.7895	Intermediate Similarity	NPC149371
0.7882	Intermediate Similarity	NPC475690
0.7882	Intermediate Similarity	NPC229825
0.7882	Intermediate Similarity	NPC173609
0.7875	Intermediate Similarity	NPC269206
0.7875	Intermediate Similarity	NPC295633
0.7875	Intermediate Similarity	NPC58956
0.7872	Intermediate Similarity	NPC288876
0.7865	Intermediate Similarity	NPC83423
0.7865	Intermediate Similarity	NPC474032
0.7857	Intermediate Similarity	NPC281132
0.7857	Intermediate Similarity	NPC223904
0.7857	Intermediate Similarity	NPC233377
0.7848	Intermediate Similarity	NPC67183
0.7841	Intermediate Similarity	NPC471738
0.7831	Intermediate Similarity	NPC121200
0.7826	Intermediate Similarity	NPC475659
0.7821	Intermediate Similarity	NPC218477
0.7816	Intermediate Similarity	NPC474369
0.7816	Intermediate Similarity	NPC28887
0.7816	Intermediate Similarity	NPC165162
0.7816	Intermediate Similarity	NPC137033
0.7816	Intermediate Similarity	NPC215364
0.7805	Intermediate Similarity	NPC474447
0.7805	Intermediate Similarity	NPC271070
0.7805	Intermediate Similarity	NPC123360
0.7805	Intermediate Similarity	NPC266119
0.7802	Intermediate Similarity	NPC162205
0.7802	Intermediate Similarity	NPC476049
0.7802	Intermediate Similarity	NPC295204
0.7802	Intermediate Similarity	NPC273579
0.7802	Intermediate Similarity	NPC288240
0.7791	Intermediate Similarity	NPC53867
0.7791	Intermediate Similarity	NPC59097
0.7791	Intermediate Similarity	NPC170377
0.7791	Intermediate Similarity	NPC475989
0.7789	Intermediate Similarity	NPC164598
0.7789	Intermediate Similarity	NPC474339
0.7789	Intermediate Similarity	NPC47880
0.7778	Intermediate Similarity	NPC474232
0.7778	Intermediate Similarity	NPC15499
0.7778	Intermediate Similarity	NPC117746
0.7778	Intermediate Similarity	NPC294434
0.7778	Intermediate Similarity	NPC469368
0.7778	Intermediate Similarity	NPC259599
0.7778	Intermediate Similarity	NPC474551
0.7778	Intermediate Similarity	NPC71533
0.7778	Intermediate Similarity	NPC474758
0.7778	Intermediate Similarity	NPC140287
0.7778	Intermediate Similarity	NPC106510
0.7778	Intermediate Similarity	NPC51486
0.7766	Intermediate Similarity	NPC141191
0.7765	Intermediate Similarity	NPC52861
0.7765	Intermediate Similarity	NPC79277
0.7765	Intermediate Similarity	NPC141810
0.7765	Intermediate Similarity	NPC475481
0.7765	Intermediate Similarity	NPC281949
0.7765	Intermediate Similarity	NPC25684
0.7765	Intermediate Similarity	NPC301477
0.7753	Intermediate Similarity	NPC227379
0.7753	Intermediate Similarity	NPC153805
0.7753	Intermediate Similarity	NPC475902
0.7753	Intermediate Similarity	NPC474471
0.775	Intermediate Similarity	NPC163003
0.775	Intermediate Similarity	NPC129665
0.7742	Intermediate Similarity	NPC184065
0.7742	Intermediate Similarity	NPC279621
0.7742	Intermediate Similarity	NPC473291
0.7742	Intermediate Similarity	NPC473859
0.7742	Intermediate Similarity	NPC185553
0.7738	Intermediate Similarity	NPC98557
0.7738	Intermediate Similarity	NPC472965
0.7738	Intermediate Similarity	NPC167881
0.7738	Intermediate Similarity	NPC63649
0.7738	Intermediate Similarity	NPC113363
0.7738	Intermediate Similarity	NPC264227
0.7727	Intermediate Similarity	NPC164393
0.7727	Intermediate Similarity	NPC472009
0.7727	Intermediate Similarity	NPC116575
0.7727	Intermediate Similarity	NPC50637
0.7722	Intermediate Similarity	NPC477448
0.7722	Intermediate Similarity	NPC477449
0.7722	Intermediate Similarity	NPC151481
0.7722	Intermediate Similarity	NPC265574
0.7717	Intermediate Similarity	NPC148463
0.7717	Intermediate Similarity	NPC476267
0.7717	Intermediate Similarity	NPC140543
0.7717	Intermediate Similarity	NPC53685
0.7711	Intermediate Similarity	NPC470240
0.7711	Intermediate Similarity	NPC281296
0.7711	Intermediate Similarity	NPC41780
0.7711	Intermediate Similarity	NPC476794
0.7711	Intermediate Similarity	NPC65603

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC85772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1759
0.2-0.3	3729
0.3-0.4	2308
0.4-0.5	802
0.5-0.6	304
0.6-0.7	56
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7978	Intermediate Similarity	NPD5785	Approved
0.7816	Intermediate Similarity	NPD5363	Approved
0.7674	Intermediate Similarity	NPD5209	Approved
0.7471	Intermediate Similarity	NPD4270	Approved
0.7471	Intermediate Similarity	NPD4269	Approved
0.7447	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7154	Phase 3
0.7356	Intermediate Similarity	NPD5369	Approved
0.7333	Intermediate Similarity	NPD5786	Approved
0.7273	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4252	Approved
0.7222	Intermediate Similarity	NPD1694	Approved
0.7222	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD46	Approved
0.7204	Intermediate Similarity	NPD6698	Approved
0.7191	Intermediate Similarity	NPD5362	Discontinued
0.7128	Intermediate Similarity	NPD7983	Approved
0.7059	Intermediate Similarity	NPD8039	Approved
0.7053	Intermediate Similarity	NPD5778	Approved
0.7053	Intermediate Similarity	NPD5779	Approved
0.7019	Intermediate Similarity	NPD6371	Approved
0.6897	Remote Similarity	NPD4756	Discovery
0.6893	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6435	Approved
0.6869	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4225	Approved
0.6854	Remote Similarity	NPD4820	Approved
0.6854	Remote Similarity	NPD4821	Approved
0.6854	Remote Similarity	NPD4819	Approved
0.6854	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4822	Approved
0.6842	Remote Similarity	NPD7838	Discovery
0.6837	Remote Similarity	NPD7839	Suspended
0.6789	Remote Similarity	NPD7115	Discovery
0.6737	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5370	Suspended
0.6737	Remote Similarity	NPD6101	Approved
0.6707	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5368	Approved
0.6633	Remote Similarity	NPD5282	Discontinued
0.663	Remote Similarity	NPD5331	Approved
0.663	Remote Similarity	NPD5332	Approved
0.6629	Remote Similarity	NPD4268	Approved
0.6629	Remote Similarity	NPD4271	Approved
0.6598	Remote Similarity	NPD6411	Approved
0.6598	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4790	Discontinued
0.6562	Remote Similarity	NPD1695	Approved
0.6471	Remote Similarity	NPD6648	Approved
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD7640	Approved
0.6465	Remote Similarity	NPD7748	Approved
0.6429	Remote Similarity	NPD5693	Phase 1
0.6429	Remote Similarity	NPD7637	Suspended
0.6421	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD7521	Approved
0.6421	Remote Similarity	NPD7334	Approved
0.6421	Remote Similarity	NPD6409	Approved
0.6421	Remote Similarity	NPD4249	Approved
0.6421	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD5330	Approved
0.6408	Remote Similarity	NPD5344	Discontinued
0.64	Remote Similarity	NPD5695	Phase 3
0.6386	Remote Similarity	NPD7341	Phase 2
0.6383	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7638	Approved
0.6355	Remote Similarity	NPD6686	Approved
0.6354	Remote Similarity	NPD4251	Approved
0.6354	Remote Similarity	NPD4250	Approved
0.6354	Remote Similarity	NPD3573	Approved
0.6296	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD6903	Approved
0.6289	Remote Similarity	NPD5737	Approved
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6647	Phase 2
0.6275	Remote Similarity	NPD6084	Phase 2
0.6275	Remote Similarity	NPD6083	Phase 2
0.6275	Remote Similarity	NPD7902	Approved
0.6265	Remote Similarity	NPD3197	Phase 1
0.6263	Remote Similarity	NPD7515	Phase 2
0.6262	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD6422	Discontinued
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4623	Approved
0.6234	Remote Similarity	NPD3172	Approved
0.6214	Remote Similarity	NPD5696	Approved
0.6204	Remote Similarity	NPD6881	Approved
0.6204	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD6011	Approved
0.62	Remote Similarity	NPD6399	Phase 3
0.6195	Remote Similarity	NPD7500	Approved
0.6182	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4266	Approved
0.6154	Remote Similarity	NPD3194	Approved
0.6154	Remote Similarity	NPD3196	Approved
0.6154	Remote Similarity	NPD3195	Phase 2
0.6147	Remote Similarity	NPD6413	Approved
0.6147	Remote Similarity	NPD6012	Approved
0.6147	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD6013	Approved
0.6145	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7900	Approved
0.6129	Remote Similarity	NPD4695	Discontinued
0.6126	Remote Similarity	NPD6053	Discontinued
0.6118	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5281	Approved
0.61	Remote Similarity	NPD5694	Approved
0.61	Remote Similarity	NPD5284	Approved
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6087	Remote Similarity	NPD3732	Approved
0.6082	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5909	Discontinued
0.6071	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6080	Approved
0.6061	Remote Similarity	NPD6904	Approved
0.6061	Remote Similarity	NPD6673	Approved
0.6047	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3666	Approved
0.6042	Remote Similarity	NPD3133	Approved
0.6042	Remote Similarity	NPD3665	Phase 1
0.6038	Remote Similarity	NPD5211	Phase 2
0.6036	Remote Similarity	NPD6617	Approved
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6869	Approved
0.6036	Remote Similarity	NPD6650	Approved
0.6036	Remote Similarity	NPD6649	Approved
0.6024	Remote Similarity	NPD4191	Approved
0.6024	Remote Similarity	NPD4192	Approved
0.6024	Remote Similarity	NPD4193	Approved
0.6024	Remote Similarity	NPD4194	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6017	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD5207	Approved
0.5983	Remote Similarity	NPD8516	Approved
0.5983	Remote Similarity	NPD8513	Phase 3
0.5983	Remote Similarity	NPD8515	Approved
0.5983	Remote Similarity	NPD8517	Approved
0.5982	Remote Similarity	NPD6882	Approved
0.5982	Remote Similarity	NPD8297	Approved
0.5974	Remote Similarity	NPD6927	Phase 3
0.5974	Remote Similarity	NPD28	Approved
0.5974	Remote Similarity	NPD29	Approved
0.5963	Remote Similarity	NPD5701	Approved
0.596	Remote Similarity	NPD5208	Approved
0.5957	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6050	Approved
0.5941	Remote Similarity	NPD6079	Approved
0.5938	Remote Similarity	NPD6110	Phase 1
0.593	Remote Similarity	NPD3704	Approved
0.5926	Remote Similarity	NPD5141	Approved
0.5922	Remote Similarity	NPD4629	Approved
0.5922	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5210	Approved
0.5918	Remote Similarity	NPD3618	Phase 1
0.5918	Remote Similarity	NPD5279	Phase 3
0.5918	Remote Similarity	NPD5690	Phase 2
0.5909	Remote Similarity	NPD7320	Approved
0.59	Remote Similarity	NPD6051	Approved
0.59	Remote Similarity	NPD4753	Phase 2
0.5897	Remote Similarity	NPD6319	Approved
0.5888	Remote Similarity	NPD7632	Discontinued
0.5882	Remote Similarity	NPD7830	Approved
0.5882	Remote Similarity	NPD7829	Approved
0.5865	Remote Similarity	NPD5221	Approved
0.5865	Remote Similarity	NPD4228	Discovery
0.5865	Remote Similarity	NPD5222	Approved
0.5865	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6372	Approved
0.5856	Remote Similarity	NPD6373	Approved
0.5849	Remote Similarity	NPD5286	Approved
0.5849	Remote Similarity	NPD4696	Approved
0.5849	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD3667	Approved
0.5833	Remote Similarity	NPD368	Approved
0.5833	Remote Similarity	NPD4223	Phase 3
0.5825	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD1696	Phase 3
0.581	Remote Similarity	NPD5173	Approved
0.5804	Remote Similarity	NPD2067	Discontinued
0.5804	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5223	Approved
0.5789	Remote Similarity	NPD4632	Approved
0.5785	Remote Similarity	NPD8273	Phase 1
0.5776	Remote Similarity	NPD6317	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data